Polymer nanocomposite coatings based on polyhedral oligosilsesquioxanes: route for industrial manufacturing and barrier properties
Source abstract
Abstract
A route to a large variety of functionalized POSS compounds by a two-step procedure has been developed. Up-scaling to high volume industrial applications is feasible. In the first step, an amino-functionalized silane such as 3-aminopropyltriethoxy silane is converted to amino-functionalized POSS (amine-POSS) by a sol–gel process. In the second step, the amine groups of amine-POSS are converted by state-of-the-art amine chemistry. A large number of reactants including carboxylic acids, esters, anhydrides, isocyanates, carbonates, epoxides, and acrylates as well as reactants suitable for nucleophilic substitution can be applied. Conversion of an amine-POSS with hexanoic acid leads to an amide-POSS. Amine chemistry can usually be performed under mild conditions, which suppresses degradation and/or cross-linking reactions of the amine-POSS during the conversion. MALDI-TOF mass spectroscopy and dynamic light scattering (particle size: 3–6 nm) have been applied to prove the conversion of an amine-POSS to an amide-POSS. 1H-NMR and TGA-MS prove the presence of amide-POSS and its thermal stability. Gas barrier properties of nanocomposite coatings based on functionalized POSS are characterized.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Silicone and Siloxane Chemistry · Marine Biology and Environmental Chemistry · Synthesis and properties of polymers
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (46)
Show source-provided references
1. Amerio E, Sangermano M, Colucci G, Malucelli G, Messori M, Taurino R, Fabbri P (2008) UV curing of organic-inorganic hybrid coatings containing polyhedral oligomeric silsesquioxane blocks. Macromol Mater Eng 293:700–70710.1002/mame.200800080 ↗
2. Beheshti N, Zhu K, Kjøniksen A, Nyström B (2008) Interaction behaviors in aqueous solutions of negatively and positively charged hydrophobically modified hydroxyethylcellulose in the presence of an anionic surfactant. Colloids Surf A Physicochem Eng Asp 328(1–3):79–8910.1016/j.colsurfa.2008.06.030 ↗
3. Chu B (1991) Laser light scattering: basic principles and practice. Academic Press, Boston
4. Cordes DB, Lickiss PD, Rataboul F (2010) Recent developments in the chemistry of cubic polyhedral oligosilsesquioxanes. Chem Rev 110:2081–217310.1021/cr900201r ↗
5. dell’ Erba IE, Williams RJJ (2008) Epoxy networks modified by multifunctional polyhedral oligomeric silsesquioxanes (POSS) containing amine groups. J Therm Anal Calorim 93(1):95–10010.1007/s10973-007-8805-1 ↗
6. dell’ Erba IE, Fasce DP, Williams RJJ, Erra-Balsells R, Fukuyama Y, Nonami H (2003) Poly(silsesquioxanes) derived from the hydrolytic condensation of organotrialkoxysilanes containing hydroxyl groups. J Organomet Chem 686:42–5110.1016/S0022-328X(03)00377-2 ↗
7. Fina A, Bocchini S, Camino G (2008) Catalytic fire retardant nanocomposites. Polym Degrad Stab 93:1647–165510.1016/j.polymdegradstab.2008.05.027 ↗
8. Glodek TE, Boyd SE, McAninch IM, La Scala JJ (2008) Properties and performance of fire resistant eco-composites using polyhedral oligomeric silsesquioxane (POSS) fire retardants. Compos Sci Technol 68:2994–300110.1016/j.compscitech.2008.06.019 ↗
9. Haas K, Rose K (2003) Hybrid inorganic/organic polymers with nanoscale building blocks: precursors, processing, properties and applications. Rev Adv Mater Sci 5:47–52
10. Helland T, Marstokk O, Männle F, Simon CR, Yang J (2009) Binder for air-drying paint comprising nanoparticle organically modified metal oxides. WO2009113876
11. Iwamuraa T, Adachib K, Sakaguchia M, Chujo Y (2009) Synthesis of organic–inorganic polymer hybrids from poly(vinyl chloride) and polyhedral oligomeric silsesquioxane via CH/π interaction. Prog Org Coat 64:124–12710.1016/j.porgcoat.2008.08.035 ↗
12. Kannan RY, Salacinski HJ, Butler PE, Seifalian AM (2005) Polyhedral oligomeric silsesquioxane nanocomposites: the next generation material for biomedical applications. Acc Chem Res 38(11):879–88410.1021/ar050055b ↗
13. Kidane AG, Edirisinghe MJ, Bonhoeffer P, Seifalian AM (2007) Flow behaviour of a POSS biopolymer solution. Biorheology 44:265–272
14. Kim KH-U, Bang YH, Choi SM, Yoon KH (2008) Polyhedral oligomeric silsesquioxane-reinforced polyurethane acrylate. Compos Sci Technol 68(13):2739–274710.1016/j.compscitech.2008.05.020 ↗
15. Kim EH, Myoung SW, Jung YG, Paik U (2009) Morphology and mechanical properties of PET by incorporation of amine-polyhedral oligomeric silsesquioxane. Prog Org Coat 64(2–3):205–20910.1016/j.porgcoat.2008.07.026 ↗
16. Li H, Yu D, Zhang JQ (2005) A novel and facile method for direct synthesis of cross-linked polysiloxanes by anionic ring-opening copolymerization with Ph12-POSS/D4/Ph8D4. Polymer 46(14):5317–532310.1016/j.polymer.2005.04.028 ↗
17. Li Q, Hutcheson SA, McKenna GB, Simon SL (2008) Viscoelastic properties and residual stresses in polyhedral oligomeric silsesquioxane-reinforced epoxy matrices. Polym Sci Polym Phys 46(24):2719–273210.1002/polb.21609 ↗
18. Lichtenhan JD, Otonari YA, Cam MJ (1995) Linear hybrid polymer building blocks: methacrylate-functionalized polyhedral oligomeric silsesquioxane monomers and polymers. Macromolecules 28(24):8435–843710.1021/ma00128a067 ↗
19. Limbach HH (2007) Single and multiple hydrogen/deuterium transfer reactions in liquids and solids. In: Hynes JT, Klinman J, Limbach HH, Schowen RL (eds) Hydrogen transfer reactions, vol 1. Wiley-VCH, Weinheim, pp 135–221 and references cited therein10.1002/9783527611546.ch6 ↗
20. Liu YR, Huang YD, Liu L (2008) Influence of methacryl polyhedral oligomeric silsesquioxane on the thermal and mechanical properties of methylsilicone resin. J Appl Polym Sci 110(5):2989–299510.1002/app.28425 ↗
21. Mabry JM, Vij A, Iacono ST, Viers BD (2008) Fluorinated polyhedral oligomeric silsesquioxanes (F-POSS). Angew Chem Int Ed 47(22):4137–414010.1002/anie.200705355 ↗
22. Männle F, Simon CR, Beylich J, Redford K (2004a) Polybranched, organic/inorganic hybrid polymer and method for its manufacture. WO2005100449
23. Männle F, Simon CR, Beylich J, Larsen ÅG, Hauge RP, Kleppe EA, Rødseth KR (2004b) Polymer composition. WO2005100469
24. Männle F, Simon CR, Beylich J, Sommer B, Hinrichsen EL, Andreassen E, Olafsen K, Redford K, Didriksen T (2004c) Method for the manufacture of polybranched organic/inorganic hybrid polymers. WO2005100450
25. Männle F, Rødseth KR, Bu H (2005) Light protective additive based on organic/inorganic hybrid polymer method for its manufacture and use thereof. WO2007053024
26. Manson BW, Morrison JJ, Coupar PI, Jaffrès P-A, Morris RE (2001) Synthesis of aldehyde functionalised polyhedral oligomeric silsesquioxanes. J Chem Soc Dalton Trans 1123–112710.1039/b100568p ↗
27. Massey LK (2003) Permeability properties of plastics and elastomers: a guide to packaging and barrier materials. In: Massey LK (ed) Plastics design library. Norwich, New York
28. Pilz M, Helland T, Simon CR, Yang J, Männle F, Bu H, Marstokk O (2009a) Epoxy coatings based on nanotechnology by using organic inorganic hybrid polymers. In: Proceedings of 19th SLF Congress, Sandefjord, 07–08 Sep 2009
29. Pilz M, Männle F, Simon CR, Trevor SL, Bu H, Tanem BS (2009b) New method for improving properties of polymer composites by using organic inorganic hybrid polymers. Solid State Phenom 151:10–1610.4028/www.scientific.net/SSP.151.10 ↗
30. Sanchez-Soto M, Schiraldi DA, Illescas S (2009) Study of the morphology and properties of melt-mixed polycarbonate–POSS nanocomposites. Eur Polym J 45(2):341–35210.1016/j.eurpolymj.2008.10.026 ↗
31. Schwab JJ, Lichtenhan JD (1998) Polyhedral oligomeric silsesquioxane (POSS)-based polymers. Appl Organomet Chem 12(10/11):707–71310.1002/(SICI)1099-0739(199810/11)12:10/11<707::AID-AOC776>3.0.CO;2-1 ↗
32. Sheen Y-C, Lu C-H, Huang C-F, Kuo S-W, Chang F-C (2008) Synthesis and characterization of amorphous octakis-functionalized polyhedral oligomeric silsesquioxanes for polymer nanocomposites. Polymer 49(18):4017–402410.1016/j.polymer.2008.06.055 ↗
33. Simon CR, Männle F (2004) Epoxy resin curing agent for enhanced wear resistance and weatherability of cured materials. WO2004035675
34. Smentkowski VS, Duong HM, Tamaki R, Keenan MR, Ohlhausen JAT, Kotula PG (2006) Using time-of-flight secondary ion mass spectrometry and multivariate statistical analysis to detect and image octabenzyl-polyhedral oligomeric silsesquioxane in polycarbonate. Appl Surf Sci 253:1015–102210.1016/j.apsusc.2006.03.091 ↗
35. Su H-W, Chen W-C (2009) Preparation of nanoporous poly(methyl silsesquioxane) films using core-shell silsesquioxane as porogen. Mater Chem Phys 114(2–3):736–74110.1016/j.matchemphys.2008.10.035 ↗
36. Wan C, Zhao F, Bao X, Kandasubramanian B, Duggan M (2009) Effect of POSS on crystalline transitions and physical properties of polyamide-12. J Polym Sci B Polym Phys 47(2):121–12910.1002/polb.21620 ↗
37. Wheeler PA, Fu BX, Lichtenhan JD, Weitao J, Mathias LJ (2006) Incorporation of metallic POSS, POSS copolymers, and new functionalized POSS compounds into commercial dental resins. J Appl Polym Sci 102(3):2856–286210.1002/app.24645 ↗
38. Wu J, Mather PT (2009) POSS polymers: physical properties and biomaterials applications. Polym Rev 49(1):25–6310.1080/15583720802656237 ↗
39. Xiao Y, Lu X, Zhang X, He C (2010) Synthesis and optical characteristics of organic light-emitting dot based on well-defined octa-functionalized silsesquioxane. J Nanopart Res 12(8):2787–279810.1007/s11051-010-9857-x ↗
40. Zhang L, Abbenhuis HCL, Yang Q, Wang Y-M, Magusin PCMM, Mezari B, van Santen RA, Li C (2007a) Mesoporous organic–inorganic hybrid materials built using polyhedral oligomeric silsesquioxane blocks. Angew Chem Int Ed 46(26):5003–500610.1002/anie.200700640 ↗
41. Zhang X, Huang Y, Wang T, Hu L (2007b) Effects of silsesquioxane coating structure on mechanical interfacial properties of carbon fibre/polyarylacetylene composites. J Mater Sci 42(13):5264–527110.1007/s10853-006-0349-4 ↗
42. Zhang Z, Gu A, Liang G, Ren P, Xie J, Wang X (2007c) Thermo-oxygen degradation mechanisms of POSS/epoxy nanocomposites. Polym Degrad Stab 92(11):1986–199310.1016/j.polymdegradstab.2007.08.004 ↗
43. Zhang Z, Liang G, Wang J, Ren P (2007d) Epoxy/POSS organic–inorganic hybrids: viscoelastic, mechanical properties and micromorphologies. Polym Compos 28(2):175–17910.1002/pc.20281 ↗
44. Zhang Z, Liang G, Wang X (2007e) The effect of POSS on the thermal properties of epoxy. Polym Bull (Heidelberg, Germany) 58(5–6):1013–102010.1007/s00289-007-0732-6 ↗
45. Zhang H-X, Shin Y-J, Yoon K-B, Lee D-H (2009) Preparation and properties of propylene/POSS copolymer with rac-Et(Ind)2ZrCl2 catalyst. Eur Polym J 45(1):40–4610.1016/j.eurpolymj.2008.09.029 ↗
46. Zhou Z, Zhang Y, Zeng Z, Zhang YJ (2008) Properties of POSS-filled polypropylene: comparison of physical blending and reactive blending. J Appl Polym Sci 110(6):3745–375110.1002/app.29007 ↗